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Holiday rentals in Middlesboro

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Top-rated holiday rentals in Middlesboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement
SUPERHOST
Entire cottage · 4 guests · 2 beds · 1 bathroom
Scenic 1 BR Cabin w/ Hiking to Hensley SettlementThe Elk Creek Cottage borders the Cumberland Gap National Historical Park property--the pathway to the west, trailblazed by Daniel Boone himself! Stay and hike to Hensley Settlement or Shillalah Creek Falls, fish for Brook-Trout, or relax with a cup of coffee on the porch surrounded by nature. Only a scenic twenty-minute drive to Middlesboro or Pineville, KY separates you from the "city." Come enjoy the peace and quiet that Elk Creek Cottage has to offer.
Studio in Historic Cumberland Gap
SUPERHOST
Entire serviced apartment · 2 guests · 1 bed · 1 bathroom
Studio in Historic Cumberland GapThis is a fully furnished studio apartment in historic Cumberland Gap, TN. It is attached to The Olde Mill Inn B&B and across from Berkau Memorial Park. Breakfast is not included in your stay (as the studio is well equipped); however, you may contact the Inn at 423-869-0868 to make reservations to have breakfast in the Inn dining room (space permitting) for a small fee. Come make yourself at home in historic Cumberland Gap, TN. Also, remember that your fur baby is also welcome to join you!
Cumberland Gap Home
Private room · 1 guest · 1 bed · 1 shared bathroom
Cumberland Gap HomeBedroom available in 3 Bdrm house in the heart of Cumberland Gap. Walking distance to national park and hiking trails and minutes from LMU. WIFI, Netflix, washer and dryer. Weekly and monthly discounts.

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Other great holiday rentals in Middlesboro

SUPERHOST
  1. Entire cabin
  2. Harrogate
Rustic Log Cabin on Powell River & Adventures🚣🏽‍♀️🎣
SUPERHOST
  1. Entire residential home
  2. Harrogate
3 bdrm ranch w/view of LMU & mountains!
  1. Entire residential home
  2. Harrogate
Moms House
  1. Entire residential home
  2. Middlesboro
Crater City Cottage
SUPERHOST
  1. Entire residential home
  2. Harrogate
Cute Bungalow across from LMU campus
  1. Entire cottage
  2. Cumberland Gap
Cozy Cumberland Gap Cottage
  1. Entire residential home
  2. Speedwell
Tackett House II
  1. Entire residential home
  2. Harrogate
Cabin on the Tolliver Manor property
  1. Entire residential home
  2. Harrogate
Harrogate Home with Mountain Views
  1. Private room
  2. Cumberland Gap
The Cabin (King with jetted tub)
  1. Private room
  2. Harrogate
Queen Room 1 within the Tolliver Manor
  1. Entire residential home
  2. Harrogate
Tolliver Manor